decasodium (2R,3S,4R,5S,6R)-3-methoxy-6-{[(2S,3R,4S,5R)-5-{[(2S,3R,4S,5R)-5-{[(2S,3R,4S,5R)-5-methoxy-3,4-bis(sulfonatooxy)oxan-2-yl]oxy}-3,4-bis(sulfonatooxy)oxan-2-yl]oxy}-2-{[(3R,4S,5R,6R)-6-methoxy-4,5-bis(sulfonatooxy)oxan-3-yl]oxy}-4-(sulfonatooxy)oxan-3-yl]oxy}-4,5-bis(sulfonatooxy)oxane-2-carboxylate

• ChemBase ID: 176273
• Molecular Formular: C29H38Na10O50S9
• Molecular Mass: 1705.06472
• Monoisotopic Mass: 1703.68941403
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](OC1)O[C@H]1[C@@H]([C@@H]([C@@H](OC1)O[C@H]1[C@@H]([C@@H]([C@@H](OC1)O[C@H]1[C@@H]([C@@H]([C@@H](OC1)OC)OS(=O)(=O)[O-])OS(=O)(=O)[O-])O[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)C(=O)[O-])OC)OS(=O)(=O)[O-])OS(=O)(=O)[O-])OS(=O)(=O)[O-])OS(=O)(=O)[O-])OS(=O)(=O)[O-])OS(=O)(=O)[O-])OS(=O)(=O)[O-])OC.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
• Canonical SMILES: CO[C@@H]1OC[C@H]([C@@H]([C@@H]1OS(=O)(=O)[O-])OS(=O)(=O)[O-])O[C@@H]1OC[C@H]([C@@H]([C@@H]1O[C@@H]1O[C@@H](C(=O)[O-])[C@@H]([C@@H]([C@@H]1OS(=O)(=O)[O-])OS(=O)(=O)[O-])OC)OS(=O)(=O)[O-])O[C@@H]1OC[C@H]([C@@H]([C@@H]1OS(=O)(=O)[O-])OS(=O)(=O)[O-])O[C@@H]1OC[C@H]([C@@H]([C@@H]1OS(=O)(=O)[O-])OS(=O)(=O)[O-])OC.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C29H48O50S9.10Na/c1-59-8-4-63-27(21(77-86(50,51)52)12(8)71-80(32,33)34)68-11-7-65-28(22(78-87(53,54)55)15(11)74-83(41,42)43)67-9-6-64-26(66-10-5-62-25(61-3)20(76-85(47,48)49)14(10)73-82(38,39)40)19(13(9)72-81(35,36)37)70-29-23(79-88(56,57)58)17(75-84(44,45)46)16(60-2)18(69-29)24(30)31;;;;;;;;;;/h8-23,25-29H,4-7H2,1-3H3,(H,30,31)(H,32,33,34)(H,35,36,37)(H,38,39,40)(H,41,42,43)(H,44,45,46)(H,47,48,49)(H,50,51,52)(H,53,54,55)(H,56,57,58);;;;;;;;;;/q;10*+1/p-10/t8-,9-,10-,11-,12+,13+,14+,15+,16-,17-,18-,19-,20-,21-,22-,23+,25-,26+,27+,28+,29+;;;;;;;;;;/m1........../s1
• InChIKey: MSJQCBORNZDNDU-WKEGHWEMSA-D

NAMES AND DATABASE IDS

Names

• IUPAC name: decasodium (2R,3S,4R,5S,6R)-3-methoxy-6-{[(2S,3R,4S,5R)-5-{[(2S,3R,4S,5R)-5-{[(2S,3R,4S,5R)-5-methoxy-3,4-bis(sulfonatooxy)oxan-2-yl]oxy}-3,4-bis(sulfonatooxy)oxan-2-yl]oxy}-2-{[(3R,4S,5R,6R)-6-methoxy-4,5-bis(sulfonatooxy)oxan-3-yl]oxy}-4-(sulfonatooxy)oxan-3-yl]oxy}-4,5-bis(sulfonatooxy)oxane-2-carboxylate
• IUPAC Traditional name: decasodium (2R,3S,4R,5S,6R)-3-methoxy-6-{[(2S,3R,4S,5R)-5-{[(2S,3R,4S,5R)-5-{[(2S,3R,4S,5R)-5-methoxy-3,4-bis(sulfonatooxy)oxan-2-yl]oxy}-3,4-bis(sulfonatooxy)oxan-2-yl]oxy}-2-{[(3R,4S,5R,6R)-6-methoxy-4,5-bis(sulfonatooxy)oxan-3-yl]oxy}-4-(sulfonatooxy)oxan-3-yl]oxy}-4,5-bis(sulfonatooxy)oxane-2-carboxylate
• Synonyms: Xylan Hydrogen Sulfate Sodium Salt; SR 25493; Xylan Polysulfate Sodium; Xylan Sulfate Sodium; Xylofuranan Sulfate Sodium; (1→4)-β-D-Xylan 2,3-Bis(Hydrogen Sulfate) Sodium; Sodium Xylan Polysulfate; Fibrase; Fibrezym; Pentosan Polysulfate Sodium Salt

Database IDs

• CAS Number: 37319-17-8
• PubChem SID: 164232183
• PubChem CID: 71751489

CALCULATED PROPERTIES

• Acid pKa: -3.2142618
• H Acceptors: 41
• H Donor: 0
• LogD (pH = 5.5): -23.761192
• LogD (pH = 7.4): -23.761206
• Log P: -4.750016
• Molar Refractivity: 246.5156 cm^3
• Polarizability: 109.997894 Å^3
• Polar Surface Area: 748.76 Å^2
• Rotatable Bonds: 30
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P227325

Pentosan polysulfate preserves renal autoregulation in ANG II-infused hypertensive rats. Angiotensin II hypertension antiinflammatory.

REFERENCES

• Inscho, E., et al.: J. Clin. Invest., 112, 1895 (2003)
• Bidani, A., et al.: Hypertension, 44, 595 (2003)
• Abbracchio, M., et al.: Pharmacol. Rev., 58, 281 (2003)